Acetate → Methyl 5-(4-fluorophenyl)-6-hydroxynicotinate

HRID 688199Notes

Reaction equation

HRID 688199 reaction equation
[Br:1][c:2]1[cH:3][c:4]([C:9](=[O:10])[O:11][CH3:12])[cH:5][nH:6][c:7]1=[O:8].[CH:58]([NH:59][CH:60]([CH3:61])[CH3:62])([CH3:63])[CH3:64].[Na+:23].[Na+:56].[Na+:57].[O-:72][C:73]([CH3:74])=[O:75].[O-:76][C:77]([CH3:78])=[O:79].[O:65]=[CH:66][N:67]([CH3:68])[CH3:69].[OH2:24].[OH2:70].[OH:13][B:14]([OH:15])[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1.[Pd+2:71].[S:25]([c:26]1[cH:27][c:28]([P:29]([c:30]2[cH:31][cH:32][cH:33][c:34]([S:35]([O-:36])(=[O:37])=[O:38])[cH:39]2)[c:40]2[cH:41][cH:42][cH:43][c:44]([S:45]([O-:46])(=[O:47])=[O:48])[cH:49]2)[cH:50][cH:51][cH:52]1)([O-:53])(=[O:54])=[O:55]>>[c:2]1(-[c:16]2[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]2)[cH:3][c:4]([C:9](=[O:10])[O:11][CH3:12])[cH:5][nH:6][c:7]1=[O:8]

Participants

10

Reactant 9

HCID 175Acetate2×HCID 923Sodium ion3×HCID 962Water2×HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)HCID 2856454-Fluorophenylboronic acidHCID 2764315Methyl 5-bromo-6-hydroxynicotinateHCID 3675707Tris(3-sulfonatophenyl) phosphine

Product 1

HCID 67339481Methyl 5-(4-fluorophenyl)-6-hydroxynicotinate

Sources & evidence

ORD record
ord-2c9f163dae494ee0ba011a3459644cab
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (3/10)

Reaction notes

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